Kinetics of the reactions of phenyl 2,4,6-trinitrophenyl ether with piperidine, n-butylamine, aniline, benzylamine, and morpholine in benzene

The kinetics of the reactions of phenyl 2,4,6-trinitrophenyl ether with piperidine, n-butylamine, benzylamine, and morpholine have been investigated as a function of the amine concentration in benzene and the results compared with that of aniline. Base-catalysis was observed with all the amines except n-butylamine. The overall reaction with morpholine was wholly base-catalysed. Mechanisms are proposed for the uncatalysed and the catalysed decomposition of the intermediate formed in nucleophilic aromatic substitution.